cis-Astringin

Details

• Internal ID: 3a462a0c-e8dd-42de-b4b8-30457a35aa5b
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C\C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• InChI: InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1-/t16-,17-,18+,19-,20-/m1/s1
• InChI Key: PERPNFLGJXUDDW-BUFXCDORSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.12638228 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• CHEBI:76157
• (Z)-astringin
• Z-ASTRINGIN
• CHEMBL469920
• Q27145794
• 3-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside
• (2S,3R,4S,5S,6R)-2-[3-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7283	72.83%
Caco-2	-	0.9100	91.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5553	55.53%
OATP2B1 inhibitior	+	0.5735	57.35%
OATP1B1 inhibitior	+	0.9560	95.60%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6568	65.68%
P-glycoprotein inhibitior	-	0.8202	82.02%
P-glycoprotein substrate	-	0.9602	96.02%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	+	0.5829	58.29%
CYP2D6 substrate	-	0.8242	82.42%
CYP3A4 inhibition	-	0.8471	84.71%
CYP2C9 inhibition	-	0.8424	84.24%
CYP2C19 inhibition	-	0.8155	81.55%
CYP2D6 inhibition	-	0.9002	90.02%
CYP1A2 inhibition	-	0.9137	91.37%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.5561	55.61%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8280	82.80%
Skin irritation	-	0.8338	83.38%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4311	43.11%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.7594	75.94%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7401	74.01%
Acute Oral Toxicity (c)	III	0.6964	69.64%
Estrogen receptor binding	+	0.5613	56.13%
Androgen receptor binding	+	0.5932	59.32%
Thyroid receptor binding	+	0.7230	72.30%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6746	67.46%
PPAR gamma	+	0.7798	77.98%
Honey bee toxicity	-	0.6885	68.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8707	87.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.09%	91.49%
CHEMBL3194	P02766	Transthyretin	94.72%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.06%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.35%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	91.20%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.22%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.13%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.40%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.19%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.11%	95.56%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.57%	92.68%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.38%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.98%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.81%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.87%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.70%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.61%	95.83%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.19%	80.78%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Picea abies
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 16040016
• NPASS: NPC203230
• ChEMBL: CHEMBL469920
• LOTUS: LTS0251851
• wikiData: Q27145794